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Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells

1
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China
2
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore 637459, Singapore
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School of Chemical and Biomolecular Engineering, The University of Sydney, Sydney 2006, Australia
*
Author to whom correspondence should be addressed.
Current address: Singapore Membrane Technology Center (SMTC), Nanyang Environment and Water Research Institute, Nanyang Technological University, Singapore 637141, Singapore
Polymers 2018, 10(5), 559; https://doi.org/10.3390/polym10050559
Received: 23 April 2018 / Revised: 16 May 2018 / Accepted: 22 May 2018 / Published: 22 May 2018
Based on simple mixing and polymerization of a hydroxyl-containing derivative of perylene bisimide (PBI) and l-malic acid, here, we demonstrate a new type of dye-polymer conjugate, PBI-poly(α,β-malic acid) (PBI–PMA). Benefiting from the excellent water-solubility of weak polyanionic PMA structure and the high fluorescence of PBI, the PBI-PMA conjugates readily dissolve in water, displaying strong pH-dependent fluorescence with the highest intensity at pH 6. Due to the excellent biocompatibility of PMA, those conjugates showed low cytotoxicity on L929 cells. Using L929 and HeLa cells, we also confirmed that the PBI-PMA-labeled cells display intense fluorescence. Overall, the PBI-PMA conjugate demonstrates high potential as a cell labeling agent with its synthesis ease, good solubility in aqueous medium, low cytotoxicity, and high fluorescence. View Full-Text
Keywords: facile synthesis; perylene bisimide; poly(α,β-malic acid); cell labeling; fluorescence facile synthesis; perylene bisimide; poly(α,β-malic acid); cell labeling; fluorescence
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MDPI and ACS Style

He, J.; Chen, H.; Guo, Y.; Wang, L.; Zhu, L.; Karahan, H.E.; Chen, Y. Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells. Polymers 2018, 10, 559. https://doi.org/10.3390/polym10050559

AMA Style

He J, Chen H, Guo Y, Wang L, Zhu L, Karahan HE, Chen Y. Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells. Polymers. 2018; 10(5):559. https://doi.org/10.3390/polym10050559

Chicago/Turabian Style

He, Ji; Chen, Huixin; Guo, Yanjia; Wang, Liang; Zhu, Lingli; Karahan, H. E.; Chen, Yuan. 2018. "Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells" Polymers 10, no. 5: 559. https://doi.org/10.3390/polym10050559

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